Jillian Medoff is an award-winning corporate writer with a record of success in developing communications programs that help organizations achieve large-scale change. She has a proven ability to formulate powerful business strategies, supervise project teams, manage multiple assignments across heavily matrixed environments, and measure effectiveness. Jillian currently works as a Senior Consultant at Segal Benz.

Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I am the eldest daughter of a traveling salesman. We moved around the country 17 times by the time I was 17; I attended seven elementary schools, two junior highs, and three high schools. One consequence of moving so often was feeling like a misfit, and ten steps removed from everyone else. At the same time, I had to be independent and assertive; otherwise, I would’ve gotten lost in the shuffle. 

As the new girl, I was thrust into unfamiliar and uncomfortable situations. Now, as a writer, I’m overly attuned to other peoples’ feelings and unafraid of tackling risky material. I also spent a lot of time alone, so I read a lot. Compulsive readers often become compulsive writers. Finally, and most importantly, I was often left out or considered an afterthought when it came to birthday parties, sleepovers, and trips to the mail. So, I learned early how to face rejection, pick myself up, and move on. 

What is something you wish you would’ve realized earlier in your life?

It took me a long time to understand that rejection isn’t personal. As a novelist, I’m rejected every day, in one way or another. When I was younger, the rejection would crush me. Now bad reviews sting, but I’m able to separate myself. I have more confidence in my work. In general, however, I believe every novelist should get a few bad reviews. Bad reviews—or worse, no reviews—are humbling, and it’s important to be humbled when you’re writing fiction. 

What are bad recommendations you hear in your profession or area of expertise?

Writing fiction is a craft. Like any craft, writing successful fiction requires years of trial and error, and herculean amounts of discipline and commitment. People underestimate how much time and energy it takes to produce one book, then another, then another. 

Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?

Like many writers, I experience rejection all the time. One of my most crushing blows was about 15 years ago. My second novel, which came out in 2002, was a big disappointment. Sales were lousy; reviews were okay, but the media coverage was minimal. Basically, the book came and went in a flash. During this time, I started working on a novel that I hoped would change all this; I was desperate to get my career back on track. Six years later, I finally finished. My agent sent it out to 26 editors (maybe more) but couldn’t sell it. Though my work had been turned down lots of times before, this particular rejection flattened me. The novel had taken a long time to write, and I had imbued it with so much importance. I couldn’t write for months afterward. Eventually, maybe a year later, I started again, though I felt hesitant and insecure. Eventually, I published my third novel, I Couldn’t Love You More. Incidentally, this book was my most successful as far as copies sold. Rejection is part of the writer’s life, and there is no shame in trying and failing, but it’s a difficult, often painful, process. 

What is one thing that you do that you feel has been the biggest contributor to your success so far?

Having a career that is separate from my fiction. When my most recent novel, This Could Hurt, came out, I wrote an essay about the importance of my corporate career. For the past 30-odd years, I’ve worked in management consulting, while writing and publishing four novels. Having a life that was structured, tedious, and repetitive gave me the mental freedom to create art. My fifth, All Things Bright and Beautiful, will be published in 2022. 

 What is your morning routine?

I try to swim 3-5 times a week. There’s a pool in my neighborhood that’s open to everyone, but you have to register for a lane at 7 am. By 7:15, the lanes are all filled! So, I get up at 6:50, log on to the website, sign up for a lane, and then fall back to sleep until 7:30. Then I have the same breakfast I’ve eaten for forty years: cereal, fruit, skim milk, and black coffee. I’m at my desk by 8:15 am and work through 6:30 pm, either at my job, on a book, or, most often, a combination of both. When I’m just starting a book, it’s hard to sit for too long—maybe an hour, sometimes only 20 minutes. But when I’m close to the end, I can write for 10, 12 hours at a time. 

What habit or behavior that you have pursued for a few years has most improved your life?

Reading, definitely. I read everything and anything. I read for pleasure, but also for inspiration. As I read, I study the book to understand how it was constructed, why the writer made certain choices (point of view, setting, tone, etc.), and ways I can make my own books more successful. I write the kinds of books I want to read, which makes me more willing to revise them over and over. 

What are your strategies for being productive and using your time most efficiently?

Here are a few of my strategies for maximizing my productivity and efficiency: 

  • Author envy. Nothing is more motivating than seeing authors I know hit the bestseller lists! Many of my friends are writers, and while I’m very happy for their success—a rising tide lifts all boats—it also helps spur me on to do better. 
  • Stop right before the good part. Let’s say you’re having a great writing day; the words are flowing from your fingers. One way to ensure another great day is to stop right in the middle of your most thrilling scene. You’ll look forward to getting back to work if you’re excited to see what happens next. 
  • Reconsider using an outline. What I love best about writing novels is the joy of discovery. When I start a new book, I have only a vague idea of where I’ll end up, and no plan at all for how I’ll get there. I write the way I read, getting caught up in the characters as they reveal themselves to me.
  • Set a timer to procrastinate. After ten minutes of folding socks or reading the news, that’s it—you’re done. Time to go to work. 
  • Get off social media. It’s an endless black hole with little upside. 
  • Don’t fear rejection or failure. Were my failures painful? Sure. Am I a better writer for them? Yes, absolutely. 

What book(s) have influenced your life the most? Why?

I’ve been a voracious reader since I was a kid. I read obsessively, from literary fiction to schlocky thrillers to dense, 700-page biographies. But out of all the thousands of books I’ve loved, two have influenced my career as a novelist—Song of Solomon by Toni Morrison and Anywhere but Here by Mona Simpson

Although very different novels, Song of Solomon and Anywhere but Here examine complex family relationships, a subject that has preoccupied me since I started writing. I was lucky enough to study with both authors in graduate school. (In fact, I only applied to one MFA program (NYU) because that’s where Mona Simpson taught!) In my first year, I took a master’s class with Toni Morrison. In my second, I took a workshop with Mona, who became my thesis advisor. The thesis, originally titled The Hunters, was sold to HarperCollins in 1995, renamed Hunger Point, and published in February 1997. 

Do you have any quotes you live by or think of often?

In graduate school, I took a class with Grace Paley who said, “Write what you don’t know about what you know.” This is how I approach my own writing. I’ll take moments from my life, from my family’s life, and from strangers’ lives. I’ll look at what happened, or might typically happen (what I know), and then I’ll consider everything I don’t know about the situation (the what if’s). Novels are created by looking at one event from multiple perspectives, imagining all the possibilities, and then teasing them out.